(S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-2-amino-3-methyl-4-phenyl-but-3-en-1-ol

HRID 1911524Notes

Reaction equation

HRID 1911524 reaction equation
C(OC([N:8]1[C@@H:12]([C:13]([CH3:21])=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][C@@H:12]([C:13]([CH3:21])=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][OH:10]

Participants

4

Reactant 1

HCID 68717187(S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 68717428(S)-2-amino-3-methyl-4-phenyl-but-3-en-1-olYield 87.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-2,2-dimethyl-4-(1-methyl-2-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester (250 mg) in 4M HCl in dioxane (2 ml) was stirred at r.t. overnight. The reaction mixture was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-3-methyl-4-phenyl-but-3-en-1-ol (122 mg, 87%) as light yellow oil. MS (ISP): 177.9 ([M+H]+))

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-7a5939111ec940d1982c10ea330a61df
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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